Three species of Phragmipedium (Orchidaceae), P. calurum, P. longifolium, and P. hybrid (var. Sorcerer's Apprentice), were analyzed by high-throughput isolation. A total of 12 new (1-4, 6-10, 12, 14, 16) and five known compounds (5, 11, 13, 15, 17) were isolated from these orchids. Compounds 1-8 are stilbenes substituted with one or two 4-hydroxybenzyl moieties. This type of substitution on stilbenes is unusual and has been reported only twice. The structure elucidation was based on spectroscopic analysis.
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An Acad Bras Cienc
August 2023
State University of Londrina, Department of Agronomy, Celso Garcia Road, Km 380, 86057-970 Londrina, PR, Brazil.
The purpose of this review is to provide information on the traditional uses, phytochemical and pharmacological studies performed with species of orchids native to the Americas and the Caribbean Islands. The treatment of inflammation is the most traditional use for plants of this family, specially in Central America, while anti-inflammatory and anticancer assays are oftenly reported in pharmacological investigations. From the chemical point of view, they are sources of phenanthrenoids and stilbenes, rare secondary metabolites not commonly found in other families of plants, as well as cycloartane triterpenes, pyrrolizidine alkaloids and flavonoids.
View Article and Find Full Text PDFNaunyn Schmiedebergs Arch Pharmacol
April 2023
Department of Pharmacology and Physiology, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, 10330, Thailand.
Recently, we have isolated and identified several bioactive flavonoids and stilbenoids with potential anticancer activity from Thai orchids. In this study, we further investigated the cytotoxic and chemosensitizing activities of these phytochemicals (namely, pinocembrin, cardamonin, isalpinin, galangin, pinosylvin monomethyl ether, 2,3'-dihydroxy-5'-methoxystilbene, (E)-2,5'-dihydroxy-2'-(4-hydroxybenzyl)-3'-methoxystilbene, 2,3-dihydroxy-3',5'-dimethoxystilbene, 2,3'-dihydroxy-5,5'-dimethoxystilbene, 3,4'-dihydroxy-5-methoxystilbene and batatasin III) against breast cancer MCF7 cells and its two multidrug resistant (MDR) sublines (MCF7/DOX and MCF7/MX). Cytotoxicity was determined with MTT assay for the estimation of the half maximal cytotoxic concentrations (IC).
View Article and Find Full Text PDFJ Ethnopharmacol
November 2021
TCM and Ethnomedicine Innovation & Development International Laboratory, Innovative Material Medical Research Institute, School of Pharmacy, Hunan University of Chinese Medicine, Changsha, 410208, PR China. Electronic address:
Molecules
May 2021
Department of Chemistry, Organic Chemistry Section, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, Germany.
The biological activities of shancigusin C () and bletistrin G (), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C () was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G () was achieved by the Wittig olefination followed by several regioselective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry.
View Article and Find Full Text PDFPlanta Med
June 2020
Natural Products Research Group, Department of Chemistry, University of Surrey, Guildford, United Kingdom.
Five compounds, 3,4'-dihydroxy-3',5,5'-trimethoxydihydrostilbene, 1: ; 3,4'-ihydroxy-3',5'-dimethoxydihydrostilbene, 2: ; 3,4'-dihydroxy-5,5'-dimethoxydihydrostilbene, 3: ; 9,10-dihydro-2,7-dihydroxy-4,6-dimethoxyphenanthrene, 4: ; and the previously unreported 1,2,6,7-tetrahydroxy-4-methoxyphenanthrene, 5: were isolated from the South American orchid, An in-depth analysis of their vascular effects was performed on rat aorta rings and tail main artery myocytes. Compounds 1: - 4: were shown to possess vasorelaxant activity on rings pre-contracted by the receptor agonist phenylephrine, the Ca1.2 stimulator (S)-(-)-Bay K 8644, or depolarized with high K concentrations.
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